Reserve funds should handle a major cap x like a roof, plus money to pay the bills while the work is being done as a tenant likely won’t be paying during this time.

Now the minimum standards your basement has to hit for it to be able to count as assessed sqft not estimated is a height of 7 ft, a point of egress (bilco doors) and a window usually in the rear, It's one of those things where if your going to go through the process of digging out a basement you might as well go for it and dig it deeper then 7 and closer to 8 ft so you actually stand out compared to the competition.Now the other side of this coin which I would suggest is if you're willing to spend 40-50k on a basement dig, consider adding a 3rd story addition if your a 2 story (think master suite, walk in closet, master bath) or an addition off the back and add a roof deck if your a 3 story (either master suite or just additional bedroom).

Also note that letting this resident in, when she doesn't meet other aspects of your criteria, could be used against you in a future FHA complaint with another protected class.

Do your own roofing. 

One of my favorite aspects is the $49 a month "Piece of Mind" package.

I'm definitely new and I don't have all the logistics planned out this is just the vision now I'm trying to backwards engineer and figure out my steps I thought my first step would be to househack a 4-Plex on an FHA loan and then graduate to six or 12 units and then move on to bigger properties most likely outside of Chicago to your point. right now I am very confused this is the second time someone has said that four unit is not like a six or 12 but I'm not really sure in what ways is it the underwriting is it the management is it literally every aspect of it.

Any other possitive factors  - stable tenant base  - alarm systems  - regular checks on the property  - no pets  - Lead safe certification  - newer roof, plumbing, electric, etc..Anything to balance off the lossesBe prepared that it may end up in a non-standard (surplus lines) market for a couple of years.If you did not have flood coverage before, see if they will continue the current policy if you get Flood coverage and increase the property coverage deductible. 

If you don't have sponsorship, by definition you don't have a deal - full stop. in some aspects, but but I'd argue in development you have to find land and partners at the same time. you have to have a competitive advantage and local knowledge. may not apply and probably different sectors. we break development up into multiple raises like Series A, Series B, etc in venture debt and discount equity tranches based on what stage the investor comes in for higher returns it's earlier like when we are investing in engineering services etc we recapitalize and spend our money with an equity sale and recapitalization. structured finance is so interesting 

Capital expenses (a new roof, HVAC, etc), maintenance (clogged drain, water leak, etc), and for vacancy. 

Equity splits, fees, preferred returns..all important aspects of underwriting and structuring a syndication deal.I first recommend starting with an underwriting model that is built to underwrite syndicated deals.